3-Hydroxy-5-methoxybenzaldehyde → HCID 67072341, compound
Reaction equation
[CH:1]1([C:4]2[C:9]([CH2:10][NH:11][CH3:12])=[CH:8][N:7]=[C:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[N:5]=2)[CH2:3][CH2:2]1.[CH2:23]([O:25][C:26]([C:28]([CH3:42])([O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:40][CH3:41])[CH:39]=1)[C:34]([OH:36])=O)[CH3:29])=[O:27])[CH3:24].OC1C=C(C=C(OC)C=1)C=O.C(CC(Br)(C)C([O-])=O)C.Cl([O-])=O.[Na+]>>[CH2:23]([O:25][C:26](=[O:27])[C:28]([O:30][C:31]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[C:33]([C:34](=[O:36])[N:11]([CH2:10][C:9]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:5][C:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)=[N:7][CH:8]=2)[CH3:12])[CH:32]=1)([CH3:29])[CH3:42])[CH3:24]Participants
6
Reactant 5
Product 1
Procedure
A] In analogy to the procedures described in example 26B] and 26C], [4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-amine (example 130C]) was reacted with 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-5-methoxy-benzoic acid (prepared from 3-hydroxy-5-methoxy-benzaldehyde [Journal of Organic Chemistry (1985), 50(13), 2236–40], by reaction with ethyl-bromoisobutyrate followed by oxidation with sodium chlorite in analogy to the procedures described in examples 52A] and 59A]) to give 2-(3-{[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethyl]-methyl-carbamoyl}-5-methoxy-phenoxy)-2-methyl-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as colorless solid.
Sources & evidence
- ORD record
- ord-7ecb13f4de514493a9b094dabd991a97
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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